Schooner Woodwind

2025 Sailing Season Has Ended, we will start sailing again mid-April 2026!

Sunset on the sails

From the 4th of July cruise. This is a photo of Woodwind sailing in the sunset just outside of Annapolis. Photo by Jeannette Ruby of California, MD

deck side view – where intentional voyages, yield exceptional views

pre-dinner deck view aboard the Woodwind II…everyone’s world, at times feels like its convulsing with change…until the Chesapeake opens canvas sails…it helps me…when I can manage to be intentional, and full present in life, that voyage…always yields an exceptional view! 🙏🏻 David Photo by David Robinson of Pittsburgh, Pennsylvania

Sailing With The Blue Angels

The Woodwind II watches the U.S. Navy Blue Angels perform in Annapolis to celebrate the 2021 U.S. Naval Academy graduation. Photo by Mike Iserman of Reston, VA

Sunset Ride

Relaxing Sunday sail in August. Beautiful sights. Photo by Genevieve Adamow of Pipersville, Pennsylvania

Woodwind at sunset

On a beautiful Friday evening in August, we set sail on Woodwind for a gorgeous view of the sunset on the Chesapeake Bay and Woodwind II doing what she does best! Photo by Mike Cashman of Madison, VA

410-263-7837